The narrative centers on the tragic romance between the Trojan prince Troilus and the widow Criseyde, set against the backdrop of the protracted Trojan War. Troilus, initially a skeptic of love, falls into a deep obsession with Criseyde, eventually securing her affection through the mediation of her uncle, Pandarus. Their clandestine relationship faces inevitable collapse when Criseyde is exchanged for a Trojan prisoner and sent to the Greek camp, where she eventually turns her affections toward the warrior Diomede. The poem, structured in five books, utilizes a third-person narrator who reflects on the instability of fortune and the fleeting nature of earthly desire.

Readers and critics frequently highlight the poem's sophisticated psychological realism, which distinguishes it from many other medieval romances. Discussion often centers on the moral ambiguity of Criseyde's actions and whether her betrayal is a result of character flaw or the pressures of her precarious situation. The balance between the lighthearted, often humorous interactions involving Pandarus and the somber, philosophical conclusion of the poem is a frequent subject of analysis. Scholars often emphasize the work's status as a foundational text in the development of English narrative poetry, noting its enduring influence on later writers. Many readers appreciate the accessibility provided by modern translations, which allow for a clearer engagement with Chaucer's complex thematic explorations of love and loss.